Hydrogen Bromide → HCID 14496389, compound

HRID 1088588Notes

Reaction equation

HRID 1088588 reaction equation
[CH2:1]([C:10]1[CH:15]=[CH:14][C:13]([C:16]2[N:21]=[CH:20][C:19]([C:22]3[CH:27]=[CH:26][C:25]([O:28]C)=[CH:24][CH:23]=3)=[CH:18][N:17]=2)=[CH:12][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].Br>C(O)(=O)C>[CH2:1]([C:10]1[CH:15]=[CH:14][C:13]([C:16]2[N:21]=[CH:20][C:19]([C:22]3[CH:23]=[CH:24][C:25]([OH:28])=[CH:26][CH:27]=3)=[CH:18][N:17]=2)=[CH:12][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 14496388HCID 14496388, compound

Product 1

HCID 14496389HCID 14496389, compoundYield 56.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 60 g of 2-(4'-nonylphenyl)-5-(4'-methoxyphenyl)pyrimidine, 240 g of hydrobromic acid and one liter of acetic acid was refluxed for 40 hours. After a large portion of acetic acid was distilled away, the residue was added to a solution of 2N sodium hydroxide. The obtained crystals were recrystallized from ethyl acetate, and 32.6 g of 2-(4'-nonylphenyl)-5-(4'-hydroxyphenyl)pyrimidine was obtained. This compound showed liquid crystal property and its phase transition temperatures were 98.4° C. at C-SA phase and 138.6° C. at SA -I phase.

Workup

  1. temperaturewas refluxed for 40 hours
  2. distillationAfter a large portion of acetic acid was distilled away
  3. additionthe residue was added to a solution of 2N sodium hydroxide
  4. customThe obtained crystals were recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-68ba6aa0d06b418fac1361f62fdef655
Source dataset
uspto-grants-1990_10
Patent number
US04963288

Reaction notes

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